Studies of N-hydroxy-N'-aminoguanidine Derivatives by Nitrogen-15 Nuclear Magnetic Resonance Spectroscopy and as Ribonucleotide Reductase Inhibitors
Abstract
Hydroxyguanidine, with the imino group of guanidine and the hydroxyamino group of hydroxyurea, has functional groups believed to be important for both anticancer and antiviral activities (Adamson, R. H. Nature (London) 1972, 236,400-401). Three new N-hydroxy-N'mninoguanidine derivatives have been synthesized and found to be 20-30 times more active than the hydroxyguanidine itself as inhibitors of ribonucleotide reductase from rat Novikoff tumors (Tai, W. A.; Lai, M. M.; Lien, E. J. "Novel -Hydroxyguanidine Derivatives as Antiviral Agents", North American Medicinal Chemistry Symposium, University of Toronto, Toronto, Canada, June 20-24,1982; Abstr, p 144). The character of the tautomeric equilibria, the pK_a values, and the protonation sites of these hydroxyguanidine derivatives have been determined by ^(15)N NMR spectroscopy.
Additional Information
© 1983 American Chemical Society. Received September 7, 1982. Publication Date: September 1983. Taken in part from the Ph.D. dissertation of A.W.T., University of Southern California, 1982. Supported in part by BRSG Grant 2S07RR 05792-05 to the USC School of Pharmacy and by the Clinical Cancer Education Program of the NCI (Grant 5R 25 CA 24426) to A.W.T. (b) Supported by the American Cancer Society (Grant CH122). (c) Supported by the National Science Foundation and by the Public Health Service (Grant No. GM-11072) from the Division of General Medical Sciences. Contribution No. 6720Additional details
- Eprint ID
- 60749
- Resolver ID
- CaltechAUTHORS:20151005-090620193
- NIH
- 2S07RR 05792-05
- National Cancer Institute
- 5R 25 CA 24426
- American Cancer Society
- CH122
- NSF
- U.S. Public Health Service (USPHS)
- GM-11072
- Created
-
2015-10-05Created from EPrint's datestamp field
- Updated
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2021-11-10Created from EPrint's last_modified field
- Other Numbering System Name
- Caltech Gates and Crellin Laboratories of Chemistry
- Other Numbering System Identifier
- 6720